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US 5,292,734 AGranted
Angiotensin II receptor blocking 2,3,6 substituted quinazolinones
AssigneeAmerican Cyanamid Company
InventorsJeremy I. Levin, Aranapakam M. Venkatesan
Life of this patent
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Abstract
This disclosure describes novel 2, 3, 6 substituted quinazolinones having the formula: ##STR1## wherein X, R, and R.sup.6 are described in the specification which have activity as angiotensin II (AII) antagonists.
Claims22
A quinazolinone compound having the formula:
- ##STR30## wherein:
- R is ##STR31## --CO.sub.2 H or --NHSO.sub.2 CF.sub.3 ;
- X is lower alkyl of 3 to 5 carbon atoms;
- R.sup.6 is:
- ##STR32## R.sup.1 is H, lower alkyl of 1 to 4 carbon atoms (optionally substituted with --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --N(R.sup.7)(R.sup.13), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br)), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), pyridinyl, thienyl, furyl --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --CON(R.sup.7)(R.sup.13), --CF.sub.3, --SPh, --N(R.sup.7)(R.sup.13), or ##STR33## R.sup.2 is H, lower alkyl of 1 to 4 carbon atoms (optionally substituted with --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --N(R.sup.7)(R.sup.13), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br)), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), pyridinyl, thienyl, furyl --CO.sub.2 R.sup.7, --CN, --CON(R.sup.7)(R.sup.13), or ##STR34## R.sup.3 is H, lower alkyl of 1 to 4 carbon atoms, phenyls substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), pyridinyl, theinyl, furyl, --CO.sub.2 R.sup.7, --CON(R.sup.7)(R.sup.13), --CN, --NO.sub.2, or ##STR35## R.sup.4 is H, --CO.sub.2 R.sup.7, --SO.sub.2 R.sup.12, lower alkyl of 1 to 4 carbon atoms, benzyl, substituted benzyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), --CON(R.sup.7)(R.sup.13) or ##STR36## R.sup.12 is phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br);
- R.sup.5 is H, lower alkyl of 1 to 4 carbon atoms;
- R.sup.7 is H, lower alkyl of 1 to 4 carbon atoms;
- R.sup.8 is H, lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), --CO.sub.2 R.sup.7 , --CH.sub.2 OH, --CN, --CON(R.sup.7)(R.sup.13) or ##STR37## R.sup.9 is H, lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br);
- R.sup.10 is H, lower alkyl of 1 to 4 carbon atoms (optionally substituted with --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --N(R.sup.7)(R.sup.13), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br)), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), pyridinyl, theinyl, furyl, --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --CON(R.sup.7)(R.sup.13), --CF.sub.3, or ##STR38## R.sup.13 is H, lower alkyl of 1 to 4 carbon atoms;
- Q is --O--, --(CR.sup.11 R.sup.14).sub.n -- or a single bond;
- Q.sup.1 is --O--, --(CR.sup.11 R.sup.14).sub.n --, ##STR39## or a single bond;
- n is 1;
- A is --(CR.sup.11 R.sup.14).sub.m --;
- m is 2;
- R.sup.11 is H, lower alkyl to 1 to 4 carbon atoms (optionally substituted with --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --N(R.sup.7)(R.sup.13), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of I to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br)), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br) pyridinyl, thienyl, furyl, --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --CON(R.sup.7)(R.sup.13), --CF.sub.3, or ##STR40## R.sup.14 is H, lower alkyl of 1 to 4 carbon atoms (optionally substituted with --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --N(R.sup.7)(R.sup.13), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of I to 3 carbon atoms, F, Cl, or Br)), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, trifluoromethyl, nitro, O-alkyl of 1 to 3 carbon atoms, F, Cl, or Br), pyridinyl, thienyl, furyl, --OR.sup.7, --CO.sub.2 R.sup.7, --CN, --CON(R.sup.7)(R.sup.13), --CF.sub.3, or ##STR41## or the pharmaceutically acceptable salts thereof.
12 more elements
Dependencies are inferred from the claim text.